Nematocidal 5-amino-5-methyl-1, 3-bis (2-ethylhexyl) hexahydropyrimidine process



Patented Sept. 18, 1962 METHYL-1,3-BIS My invention relates tonematocidal compositions. More particularly, it relates to nematocidalcompositions having as the active ingredient amino-5-rnethyl-l,3-bis(2-ethylhexyl) hexahydropyrimidine.

The wide-spread presence of nematodes in soil throughout the UnitedStates results in great economic loss each year. Various nematodesreduce the production of many of the more important crops such as wheat,sugar beets, potatoes, soybeans and citrus fruits. However, nematodesvery seldom kill the plants which they attack but deprive them of theirnormal growth. Losses thus inflicted by nematodes in this way constitutea serious economic problem.

In the past, many materials and classes of materials have beenrecommended as nematocides. A great majority of these compositions,however, have proven not to be practical nematocides due to lack ofready availability, cost, danger of application, etc. Of equal, if notgreater importance, is the fact that a particular agent may beespecially efiective against one or several types of nematodes but berelatively ineffective on other nematodes when applied in practicalquantities. Also, particular nematodes incline to become, over longperiods of time, resistant to almost every kind of known nematocide.

The eflicacy of a nematocidal composition is generally measured by theamount of the active ingredient necessary to kill all nematodes in agiven area.

I have now discovered that compositions containing 5 amino 5 methyl 1,3bis(2 ethylhexyl)hexahydropyrimidine efiectively destroy nematodes inthe soil.

The exact quantity of the above compound to be utilized in nematocidalcompositions will vary widely and to a certain extent will depend uponthe type of compositions in which the material is to be employed, methodof application and the particular nematode to be destroyed. In general,I have found that concentrations as low as one part of the abovecompound in four million parts of a carrier are sufficient to destroynematodes. For some requirements, however, stronger concentrations maybe desirable.

In utilizing the nematocidal compositions of my invention, I canincorporate the named active compound in any suitable carrier which isunreactive with the compound. Since the active compound is soluble inwater, its aqueous solution can be inexpensively and readily used.However, many different carriers including solid carriers such asdiatomaceous earth, solid fertilizers, etc., can be used. Also, manyother ingredients such as ammonia can be incorporated into thecomposition of my invention.

The composition of my invention can be applied by any suitable means.One method is by spraying an aqueous solution of the active compounddirectly on the ground. Another, when a solid carrier is desired, is bydusting the solid composition on the ground and allowing rain water ortop-dressed water to leach the active compound down into the soil.

The following examples are offered to illustrate the use fulness of mynew compositions; however, I do not intend to be limited to theparticular proportions, materials, etc., which are shown. Rather, Iintend to include equivalents within the scope of my invention evidentto those skilled in the art.

Example I On each of ten dishes 25 mm. in diameter and 15 mm. deep, thebottoms being covered with filter paper, was placed 0.6 milliliter ofegg yolk infusion. Several nematodes were then placed on each dish andkept at a temperature between 20 C. to 30 C. for five days. Ten similardishes were prepared except that the egg yolk infusion contained onepart in four million of S-amino-S-methyl-1,3-bis(2-ethylhexyl)hexahydropyrimidine. These dishes were alsokept at a temperature of between 20 C. to 30 C. for five days. At theend of the five-day period it was observed that there were large numbersof active nematodes on each of the ten dishes having egg yolk infusionwhich contained no active nematocide. However, on the ten dishes havingincorporated into the egg yolk the active composition, no nematodesremained alive.

Example II The experiment of Example I was conducted except that theactive ingredient contained in the egg yolk infusion was present in onepart in one million, instead of one part in four million. At the end ofthe five-day period there were a large number of active nematodes oneach of the ten dishes having egg yolk infusion which contained noactive nematocide. On the ten dishes having incorporated into the eggyolk infusion S-amino-S-methyl-1,3-bis(2-ethylhexyl)hexahydropyrimidine, no nematodes remained alive.

Example III The experiment of Example I was conducted except that theactive ingredient contained in the egg yolk infusion was present in onepart in 500,000 instead of one part in 4 million. At the end of thefive-day period there were a large number of active nematodes on each ofthe ten dishes having egg yolk infusion which contained no activenematocide. On the ten dishes having incorporated into the egg yolkinfusion 5-arnino-5-methyl-1,3-bis(2- ethylhexyl)hexahydropyrimidine, nonematodes remained alive.

Example I V 0.1 gram of 5-amino-5-methyl-L3-bis(Z-ethylhexyl)hexahydropyrimidine was dissolved in 10 liters of water and theresulting solution was applied to sandy loam soil which was heavilyinfested with nematodes. The degree of concentration corresponded to 50parts of the nematocidal agent per million parts by weight of soil. Atthe end of 7 days no living nematodes were observed in the thus-treatedsoil.

Now having described my invention, what I claim is:

1. The method of controlling the growth of nematodes which comprisesapplying thereto a nematocidal amount of a composition containingS-amino-S-methyl-1,3-bis(2- ethylhexyl)hexahydropyrimidine as anessential active ingredient.

2. A process for destroying nematodes in the soil which comprisesapplying directly on the soil S-amino-S-methyl-1,3-bis(Z-ethylhexyl)hexahydropyrimidine.

3. A process for destroying nematodes in the soil which comprisesapplying directly on the nematodes at least one part ofS-amino-S-methyl-1,3-bis(2-ethylhexyl)hexahydropyrimidine per fourmillion pants of soil treated.

References Cited in the file of this patent Kay: Dissertation Abstracts,vol. 16, pp. 227-228 (1956).

1. THE METHOD OF CONTROLLING THE GROWTH OF NEMATODES WHICH COMPRISES APPLYING THERETO A NEMATOCIDAL AMOUNT OF A COMPOSITION CONTAINING 5-AMINO-5-METHYL-1,3-BIS(2ETHYLHEXYL)HEXAHYDROPYRIMIDINE AS AN ESSENTIAL ACTIVE INGREDIENT. 